158496
Proton-sponge®
99%
Synonym(s):
1,8-Bis(dimethylamino)naphthalene, N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine
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About This Item
Linear Formula:
C10H6[N(CH3)2]2
CAS Number:
Molecular Weight:
214.31
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
244-001-6
Beilstein/REAXYS Number:
396782
MDL number:
Assay:
99%
Form:
solid
Quality Level
assay
99%
form
solid
mp
49-51 °C (lit.)
solubility
chloroform: soluble 50 mg/mL, clear (faint yellow to dark yellow to dark red)
functional group
amine
SMILES string
CN(C)c1cccc2cccc(N(C)C)c12
InChI
1S/C14H18N2/c1-15(2)12-9-5-7-11-8-6-10-13(14(11)12)16(3)4/h5-10H,1-4H3
InChI key
GJFNRSDCSTVPCJ-UHFFFAOYSA-N
General description
Proton-sponge is a nucleophilic base used in alkoxycarbonylation, dehydrofluorination, arylation, and intramolecular cyclization reactions.
Proton-sponge is also referred to as 1,8-dimethylamino naphthalene. It is very strong base with weak nucleophilic character due to steric effects. It also participates in the reactions between arachno-6,9-C2B8H14 and selected acyl chlorides. It has been tested as an effective H+ scavenger.
Proton-sponge is also referred to as 1,8-dimethylamino naphthalene. It is very strong base with weak nucleophilic character due to steric effects. It also participates in the reactions between arachno-6,9-C2B8H14 and selected acyl chlorides. It has been tested as an effective H+ scavenger.
Application
Proton-sponge can be used in the synthesis of C-substituted t-BuNH-8,9-R,R′-nido-7,8,9-C3B8H9 (R,R′ = H,H; MeH; Me,Me; Ph,H and Ph,Ph) tricarbollide compounds. It was also used in the preparation of saturated fluoroalkyl(hydrido) complexes of Iridium.
Very strong base with weak nucleophilic character due to steric effects.
Legal Information
Proton-sponge is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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1, 8-Bis (dimethylamino) naphthalene
Barner BA
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Mario Bakardjiev et al.
Inorganic chemistry, 52(15), 9087-9093 (2013-07-28)
Reactions between arachno-6,9-C2B8H14 (1) and selected acyl chlorides, RCOCl, in the presence of PS (PS = "proton sponge", 1,8-dimethylamino naphthalene) in CH2Cl2 for 24 h at reflux, followed by in situ acidification with concentrated H2SO4 at 0 °C, generate a
Mario Bakardjiev et al.
Dalton transactions (Cambridge, England : 2003), 39(17), 4186-4190 (2010-04-15)
Treatment of C-substituted nido dicarbadecaboranes 5,6-R',R-5,6-C(2)B(8)H(10) (1) (where R',R = H,H (1a); H,Me, (1b); Me,Me, (1c); H,Ph, (1d) and Ph,Ph, (1e) with 1,8-bis-(dimethylamino)naphthalene (proton sponge = PS) and t-BuNC in CH(2)Cl(2), followed by acidification, generated a series of pure neutral
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 158496-50G | 04061838743978 |
| 158496-10G | 04061838743961 |